Need Advice on First Time Anal Penetration

My bf and I are attempting to have anal sex. I've tried explaining to him that prepping is needed ahead of time. The only thing is he's going by what someone else told him and that is to enter all the way in to get the pain done and over with.

He's length is 6 and a half inches, and he's girth is 5 and a half inches. What would you suggest on how to go about this? Any advice would be much appreciated.

Dear H,

Tell your boyfriend it's your asshole, not his stupid friends. First time anal penetration is best done by you alone, very slowly with a well-oiled clean finger after you've stimulated your clitoris to a high level of arousal. You know, very turned on. Slow and easy while breathing and focusing on releasing the muscle. It's best to have an empty bowel so an light enema is advised with enough time for all the water to be released before proceeding which can take up to an hour or more.

Anal sex in not the bend over shove it in like your BF imagines. I'd like to shove a big dildo up his even dumber friends asshole to see how he'd like it.

You must be in charge the whole time and he must listen when you say, "Stop" and then stop. This requires a lot of trust. He should begin by kissing, licking and making love to your butty hole with his lips and tongue keeping every thing wet with saliva. Then with a well oiled finger, begin to VERY slowly penetrate with YOU directing him to STOP when it burns. At that point you focus again on relaxing and releasing your sphincter muscles. I repeat: This requires trust. Not him thinking I'll just dive in and it won't hurt anymore. That's called anal rape!

So many guys want to dive right in but I'd first demand he let you penetrate him with a finger first just so he'll know what you might be feeling. Ha! Just try and touch a dudes butt hole. Most of them go into high defense mode. So talk this out and make sure he hears what you are saying, not some jackass insensitive jerk who says "Ram it in fast."

Bottom line? Get very turned on first with clitoral stimulation. Lots of yummy organic Almond oil, (Vaseline if nothing else is available) carefully filed clean fingernails, slow and easy beginning with one finger then two and when his dick head is pressing against your rosebud, you push back into him and control the penetration while he follows your lead. My book Orgasms for Two has more details on anal sex including taking an enema. It's available from Amazon.

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I'd like to add that your position also matters a lot. While anal is not a "bend over and ram it in" kind of thing (at least not at first, haha), it's helpful for your first time to be layed down on your side and slighty over (like spooning! You being the little spoon and him being the big spoon). As long as your back is relaxed and you are comfy, you're good to go. From personal experience this is a very relaxed and comfortable position to first begin anal. Anal feels amazing. It just has to be done right. It takes two to make it work.
Have fun!

I was fifty when another man entered me for the first time. I must have been lucky, as I felt no pain, just great enjoyment from having him inside me. Since then, dozens of guys have had their cocks in my ass, and only a couple very large ones were uncomfortable at first, but once I got accustomed to them, enthusiasticly enjoyed them.